7250-28-4

Upstream product

• 108-89-4 picoline 
• 70-11-1 α-bromoacetophenone 
• 2033-24-1 cycl-isopropylidene malonate 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 769-42-6 1,3-dimethylbarbituric acid 
• 104-87-0 4-methyl-benzaldehyde 
• 3282-32-4 2-diazo-acetophenone 

Downstream Products

• 948-65-2 2-phenyl-indole 
• 73916-32-2 [2-furan-2-yl-7-methyl-1-(5-nitro-furan-2-yl)-indolizin-3-yl]-phenyl-methanone 
• 90625-69-7 (3aS,4S,9aR,9bR)-4-Benzoyl-8-methyl-2-p-tolyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione 
• 86551-95-3 (1S,5R,6S)-6-Benzoyl-1,3-dimethyl-4,5-diphenyl-bicyclo[3.1.0]hex-3-en-2-one 
• 108-89-4 picoline 
• 98-86-2 acetophenone 
• 154224-61-0 3-benzoyl-7-methylindolizine-1-carbonitrile 
• 51386-42-6 1-(3-benzoyl-7-methyl-indolizin-1-yl)-ethanone 
• 25357-50-0 4-methylpyridinium phenacylide 
• 86551-96-4 (5'-Hydroxy-4',6'-dimethyl-[1,1';2',1'']terphenyl-3'-yl)-phenyl-methanone 
• 885-91-6 2-phenyl-7-methylimidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines

An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonation/elimination/cycloisomerization is proposed.

Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones

Enantioselective diverse synthesis of a small-molecule collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asymmetric preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of N-heterocycle-containing scaffolds with functional group, and stereochemical diversity. Herein, we report a breakthrough toward this end via an initial diastereo- A nd enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations. Chiral N,N′-dioxide-earth metal complexes enable the generation of optically active tetrahydroindolizines in situ, across the strong background reaction for racemate-formation. In connection with deliberate sequential transformations, involving convenient rearomatic oxidation, and light-active aza-Norrish II rearrangement, the tetrahydroindolizine intermediates were converted into the final library including 3-arylindolizine derivatives and dicarbofunctionalized 1,5-dicarbonyl compounds. More importantly, the stereochemistry of four-stereogenic centered tetrahydroindolizine intermediates could be efficiently transferred into axial chirality in 3-arylindolizines and vicinal pyridyl and aryl substituted 1,5-diketones. In addition, densely functionalized cyclopropanes and bridged cyclic compounds were also discovered depending on the nature of the pyridinium ylides. Mechanism studies were involved to explain the stereochemistry during the reaction processes.

Facile one-pot tandem synthesis of perfluoroalkylated indolizines under metal-free mild conditions

A direct metal-free method for the synthesis of perfluoroalkylated indolizines by means of DIPEA-promoted tandem C[sbnd]N/C[sbnd]C bond formation was developed. Various substituted pyridines and bromoacetyl derivatives with methyl perfluoroalk-2-ynoates proceeded smoothly in this mild transformation, and the desired products were obtained in good to excellent yields under air.

Visible-Light-Induced Carbo-2-pyridylation of Electron-Deficient Alkenes with Pyridinium Salts

A simple and practical visible-light-induced carbo-2-pyridylation of electron-deficient alkenes with readily available N-benzoylmethylpyridinium bromides is reported. More than 40 examples are presented and proceed in greater than 80 % yield (on average)

Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant

A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.

One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K2Cr2O7 as an efficient oxidant under base free conditions

A one-pot method for synthesizing multi-substituted indolizines from α-halo-carbonyl compounds, pyridines and electron deficient alkenes was developed. A sub-equivalent amount of potassium dichromate was used as an oxidant under base free conditions. The transformation developed should be of economic efficiency.

Novel indolizine derivatives with unprecedented inhibitory activity on human farnesyltransferase

The rational structural modification of new substituted indolizin-3-yl(phenyl)methanones 1a-i, 2a-i and 3a-i has greatly improved human farnesyltransferase inhibition. The para-bromophenyl analog 2f bearing an ester unit on the indolizine ring demonstrates the highest inhibition potential, with IC50 value of 1.3 ± 0.2 μM. The amidic series 1a-i proves to be the most promising for future modulations, particularly at the triple bond level.

Regioselective CH bond activation on stabilized nitrogen ylides promoted by Pd(II) complexes: Scope and limitations

The orthopalladation of N-ylides [HxCyN-CHC-(O)Ar] (HxCyN = pyridine, benzylamine, imidazole, aniline, and phenylpyridine; Ar = aryl) has been studied. The incorporation of the Pd atom to these substrates is regioselective, since the orthopalladation is produced, in most of the cases, only at the aryl ring of the benzoyl group with concomitant C-bonding of the Nylide. The X-ray structure of one representative example is reported. Factors governing the observed orientation are discussed, because this regioselectivity is worthy of note, considering the deactivating nature of the carbonyl group. Two exceptions to the general trend have been observed. The first one is the double metalation of the ylide [PhMe2NCHC(O)Ph], which incorporates one Pd at each Ph. The second one is the palladation of the phenylpyridine derivative, which occurs at the pyridinic 2-phenyl ring and produces a six-membered palladacycle.

Microwave-assisted, one-pot three component synthesis of 2-phenyl H-imidazo[1, 2-α]pyridine

A novel synthesis of 2-phenylH-imidazio[1, 2-α] pyridines is described from a one-pot, three-component reaction between pyridine, guanidine (urea or thiourea) and α-bromoketones under microwave irradiation and solvent-free conditions in excellent yields.

Copper acetate monohydrate: A cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes

We report a highly practical one-pot method for synthesizing multi-substituted indolizines from ?±-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.